Synthesis of the First Sialic Acid Analogue Containing a y-Pyrone Moiety

1999 ◽  
Vol 52 (12) ◽  
pp. 1127 ◽  
Author(s):  
Hua Chee Ooi ◽  
B Sebastian ◽  
M. Marcuccio ◽  
W. Roy Jackson ◽  
David F. O'Keefe
Keyword(s):  
Sialic Acid ◽  
Acid Derivative ◽  
Acetylneuraminic Acid ◽  
Acid Analogue ◽  
Sialic Acid Analogue

Oxidation of the two DANA (2-deoxy-2,3-didehydro-N-acetylneuraminic acid) derivatives (3) and (4) by using several reagents has led to the isolation of the first sialic acid derivative (1) containing a γ-pyrone moiety.

scholarly journals Two different sialidases, KDN-sialidase and regular sialidase in the starfish Asterina pectinifera

1996 ◽  
Vol 315 (3) ◽  
pp. 1041-1048 ◽  
Author(s):  
Jeffrey A. YUZIUK ◽  
Hiroki NAKAGAWA ◽  
Akira HASEGAWA ◽  
Makoto KISO ◽  
Su-Chen LI ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Molecular Mass ◽  
Isoelectric Point ◽  
Competitive Inhibitor ◽  
Ph Optimum ◽  
Acetylneuraminic Acid ◽  
Acid Analogue ◽  
Competitive Inhibitors ◽  
Sialic Acid Analogue ◽  
Asterina Pectinifera

We have found the coexistence of two different sialidases in the entrails of the starfish Asterina pectinifera: a regular sialidase (RS), which cleaves sialic acid from sialoglycoconjugates, and a KDN-sialidase (KS) which releases the sialic acid analogue KDN (2-keto-3-deoxy-D-glycero-d-galacto-nononic acid) from KDN-containing glycoconjugates that are resistant to RS. The 6700-fold purified KS and 1300-fold purified RS were prepared to study the properties of these two sialidases. KS and RS from Asterina starfish differ in several properties other than glycon specificity, including molecular mass, isoelectric point (pI) and susceptibility to competitive and non-competitive inhibitors. KS has a molecular mass of 31 kDa and a pI of 8.3 while RS has a molecular mass of 128 kDa and a pI of about 4.8. 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (NeuAc2en), but not 2,3-dehydro-2-deoxy-KDN (KDN2en), is a potent competitive inhibitor of RS (Ki ~ 0.007 mM); however, both NeuAc2en and KDN2en are moderate inhibitors of KS (Ki ~ 0.04 mM). Hg2+ is a potent non-competitive inhibitor of RS but not of KS. KS and RS were examined for their ability to hydrolyse KDN- and NeuAc-containing glycoconjugates. KS hydrolyses 4-methylumbelliferyl-α-KDN (MU-KDN) 20 times faster than 4-methylumbelliferyl-α-NeuAc (MU-NeuAc), while RS hydrolyses MU-NeuAc 88 times faster than MU-KDN at the pH optimum of 4.0. KS effectively hydrolyses KDN-GM3 (where GM3 is NeuAcα2 → 3Galβ1 → 4Glcβ1-1´Cer, and Cer is ceramide), KDNα2 → 3lactose, KDNα2 → 6lactose, KDNα2 → 6N-acetylgalactosaminitol, KDNα2→6(KDNα2→3)N-acetylgalactosaminitol and KDNα2 → 6(GlcNAcβ1 → 3)N-acetylgalactosaminitol. However, under the same conditions, these KDN-containing glycoconjugates are refractory to RS. Conversely, GM3, NeuAcα2 → 3lactose and NeuAcα2 → 6lactose are effectively hydrolysed by RS but not by KS.

Total Biosynthesis of Legionaminic Acid, a Bacterial Sialic Acid Analogue

2016 ◽  
Vol 55 (39) ◽  
pp. 12018-12021 ◽  
Author(s):  
Mohamed I. Hassan ◽  
Benjamin R. Lundgren ◽  
Michael Chaumun ◽  
Dennis M. Whitfield ◽  
Brady Clark ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Acid Analogue ◽  
Sialic Acid Analogue

ChemInform Abstract: Synthesis of a Carbocyclic Sialic Acid Analogue for the Inhibition of Influenza Virus Neuraminidase.

ChemInform ◽  
2010 ◽  
Vol 32 (36) ◽  
pp. no-no
Author(s):  
Armandodoriano Bianco ◽  
Mario Brufani ◽  
Fedele Manna ◽  
Cristiana Melchioni
Keyword(s):  
Influenza Virus ◽  
Sialic Acid ◽  
Acid Analogue ◽  
Sialic Acid Analogue ◽  
Influenza Virus Neuraminidase

scholarly journals Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

2010 ◽  
Vol 6 ◽  
Author(s):  
Arne Homann ◽  
Riaz-ul Qamar ◽  
Sevnur Serim ◽  
Petra Dersch ◽  
Jürgen Seibel
Keyword(s):  
Sialic Acid ◽  
Cell Surface ◽  
Carcinoma Cell ◽  
Larynx Carcinoma ◽  
Interaction Processes ◽  
Acid Analogue ◽  
Human Larynx ◽  
Sialic Acid Analogue ◽  
Metabolic Glycoengineering ◽  
Human Larynx Carcinoma

Sialic acids are located at the termini of mammalian cell-surface glycostructures, which participate in essential interaction processes including adhesion of pathogens prior to infection and immunogenicity. Here we present the synthesis and bioorthogonal metabolic incorporation of the sialic acid analogue N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex) into the cell-surface glycocalyx of a human larynx carcinoma cell line (HEp-2) and its fluorescence labelling by click chemistry.

ChemInform Abstract: Synthesis of the First Sialic Acid Analogue Containing a γ-Pyrone Moiety.

ChemInform ◽  
2010 ◽  
Vol 31 (28) ◽  
pp. no-no
Author(s):  
Hua Chee Ooi ◽  
Sebastian M. Marcuccio ◽  
W. Roy Jackson ◽  
David F. O'Keefe
Keyword(s):  
Sialic Acid ◽  
Acid Analogue ◽  
Sialic Acid Analogue

Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase

2001 ◽  
Vol 332 (1) ◽  
pp. 23-31 ◽  
Author(s):  
Armandodoriano Bianco ◽  
Mario Brufani ◽  
Fedele Manna ◽  
Cristiana Melchioni
Keyword(s):  
Influenza Virus ◽  
Sialic Acid ◽  
Acid Analogue ◽  
Sialic Acid Analogue ◽  
Influenza Virus Neuraminidase

A convenient method for the introduction of nitrogen and sulfur at C-4 on a sialic acid analogue

1993 ◽  
Vol 244 (1) ◽  
pp. 181-185 ◽  
Author(s):  
Mark von Itzstein ◽  
Betty Jin ◽  
Wen-Yang Wu ◽  
Malcolm Chandler
Keyword(s):  
Sialic Acid ◽  
Convenient Method ◽  
Acid Analogue ◽  
Sialic Acid Analogue
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